I know exactly where you are coming from! Every time I have sold off one of my Land Rovers I have ended up looking for another within a year. The present one stays until I can no longer drive. Have thought of selling the 4/4 several times as I hardly use it, but it's now the wrong time of year, so it will get a few runs out before next spring, then we'll see. It mostly boils down to the struggle to exit (no problem entering, hood down) and the necessity of wearing a different set of (narrow) footwear so I won't use it for short trips,
100% agree with all. I am not in a rush to sell and as you say, it's not the best time of the year to do so. Plus I have seen Defender prices starting to creep down a tad. It's amazing some delivery miles examples are still making their way into the market. Let's see. I have two retailers looking to buy it but I am not holding my breath in regards to being offered a decent amount.
I also played with the idea of buying a slightly older Defender and keep the 4/4 but I'll be in the same situation, a car sat in the garage which gets washed and looked at more than driven...hehe.